Viewing 40 of 56 rentals in Chestertown
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Vacation homes - vacation rentals
14 Vacation rentals
from $365 / night
$2,555 / week
from $270 / night
$1,890 / week
from $264 / night
$1,848 / week
from $416 / night
$2,912 / week
from $243 / night
$1,701 / week
from $500 / night
$3,500 / week
from $650 / night
$4,550 / week
from $1,171 / night
$8,197 / week
from $292 / night
$2,044 / week
from $581 / night
$4,067 / week
from $592 / night
$4,144 / week
from $172 / night
$1,204 / week
from $800 / night
$5,600 / week
from $400 / night
$2,800 / week
Great rentals within 20 miles that match your search
from $458 / night
$2,863 - $4,787 / week
from $189 / night
$1,125 / week
from $350 / night
$2,450 / week
from $950 / night
$6,650 / week
from $250 / night
$1,750 / week
from $227 / night
$1,589 / week
from $395 / night
$2,765 / week
from $300 / night
$2,100 / week
from $1,486 / night
$10,402 / week
from $950 / night
$6,650 / week
from $500 / night
$3,500 / week
from $495 / night
$3,465 / week
from $261 / night
$1,827 / week
from $202 / night
$1,414 / week
from $486 / night
$3,402 / week
from $425 / night
$2,975 / week
from $709 / night
$4,963 / week
from $165 / night
$1,155 / week
from $214 / night
$1,498 / week
from $416 / night
$2,912 / week
from $627 / night
$4,389 / week
from $230 / night
$1,610 / week
from $291 / night
$2,037 / week
from $875 / night
$6,125 / week
from $1,200 / night
$8,400 / week
from $1,265 / night
$8,855 / week